Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
  • C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids

Definitions

• Alkyl ether sulfates comprise an important class of anionic surfactants particularly extensively used in shampoos and light-duty liquid detergents. These surfactants are typically prepared by sulfation of an ethoxylated long-chain alcohol to form the corresponding sulfuric acid half-ester, followed by neutralization of the remaining acid group to a corresponding salt to improve detergency. While some sulfation methods simultaneously accomplish sulfation and neutralization of the starting ethoxylated alcohol, more usually the half-ester is first formed, as for example when sulfur trioxide, sulfuric acid, oleum, or chlorosulfuric acid are used as sulfating agents. Neutralization of the product is then customarily carried out by reaction with a suitable base to form the corresponding half-ester salt.
• alkyl ether sulfate compositions are prepared by neutralization of an alkyl ether sulfuric acid half-ester of the formula
• R is C 10 -C 20 -alkyl and n is from 1 to 7, with a neutralizing agent in the presence of a polyhydroxy oligomer compound such as a polyglycerol or a hydrogenated, hydrolyzed polysaccharide, for example hydrolyzed corn syrup solids.
• a polyhydroxy oligomer compound such as a polyglycerol or a hydrogenated, hydrolyzed polysaccharide, for example hydrolyzed corn syrup solids.
• Neutralization of the sulfuric acid half ester is carried out with a neutralizing agent of the type used in prior art neutralizing processes, particularly an agent which provides an alkali metal, alkaline earth metal, alkanolamine, or ammonium salt of the sulfuric acid half-ester.
• a neutralizing agent of the type used in prior art neutralizing processes, particularly an agent which provides an alkali metal, alkaline earth metal, alkanolamine, or ammonium salt of the sulfuric acid half-ester.
• Particularly suitable neutralizing agents include potassium, sodium, or ammonium hydroxides and mono-, di-, or triethanolamine.
• the neutralization process is carried out in the presence of sufficient polyhydroxy oligomer to provide a product having an activity of at least about 45% as measured by titration with a standard cationic surfactant.
• the neutralized, alcohol-free salt is to be used in a shampoo or other viscosity dependent formulation, the use of large amounts of polyhydroxy oligomer which might adversely affect the desired viscosity characteristics of the shampoo is not recommended.
• amounts of polyhydroxy oligomer of from about 2% to 15% by weight, based on the weight of the alkyl ether sulfuric acid half-ester are employed; and preferably, amounts in the range of from about 5% to 10% by weight are employed, primarily for economic reasons. This latter narrow range is particularly suitable when the neutral sulfate is to be used in shampoos, as such amounts of polyhydroxyoligomer tend not to decrease the viscosity of typical prior art shampoo formulations.
• Suitable polyglycerols are those oligoglycerols of the type produced by dehydration of glycerol with condensation of the dehydrated monomers.
• oligoglyceroles having 2-10 glycerol groups and preferably products predominately comprising tetramers, pentamers, hexamers, or heptamers of glycerol.
• a commercially available polyglycerol useful in the practice of the invention is Polyglycerol 06, a product of Mazer Chemical Co.
• the hydrogenated, hydrolyzed corn syrup solids useful in the practice of the invention are of the type described as hydrogenated starch hydrolysates in CTGA Dictinary, 3rd Edition Supplement, 1985, p. 36.
• Other polyhydroxy oligomers the invention include cyclodextrins and alkyl polyglycosides.
• an alkyl ether sulfuric acid half ester of the above-described formula is neutralized according to the process of the invention by addition of the half-ester to an aqueous solution of the neutralizing agent and polyhydroxy oligomer.
• sodium chloride is added to necessary to increase the viscosity of the composition as desired, as is known in the prior art.
• the pH is adjusted to neutral or slightly alkaline as required, suitably with 25% NaOH or 50% citric acid, or a combination thereof.
• a neutralized alkyl ether half-ester composition according to the invention typically having an activity in excess of 50%, is obtained.
• the alkyl ether sulfuric acid half-ester neutralized according to the invention is conveniently used in shampoo formulations comprising the half-ester neutralization product as the sole or primary detergency ingredient.
• Useful shampoos include compositions comprising the neutralization product diluted with water to the desired viscosity.
• Shampoo compositions according to the invention optionally include standard ingredients such as thickeners, perfumes, foaming agents, conditioning agents, compatible auxiliary surfactants, dyes, pearlescing agents, and opacifiers.
• the half-ester (chilled) was added in a slow stream to a cooling mixture of the other components, and the pH adjusted with 25% NaOH/50% citric acid to 7.5.
• the product had an activity of 55.16% and a viscosity of 7,000 cps.
• Example IA The procedure of Example IA was followed. The pH was adjusted with 25% NaOH/50 citric acid to 7.9.
• Viscosity 7500 cps.
• the half-ester was added slowly to a cooled solution of NaCl and aqueous polyglycerol; 82 ml. NH 4 OH in H 2 O was then added. When the pH fell below 6, 10 ml. of NH 4 OH was added. 2 additional 10 ml. portions, followed by a 5 ml. portion, of NH 4 OH were further added. The reaction mixture was then mixed for 15 mins. A very thick product was obtained, having the following characteristics:
• Example 3A The procedure of Example 3A was followed, using 80 g. NH 3 and HYSTAR 5875 instead of polyglycerol. After about 1/3 of the halfester was added, the thick paste naturally formed began to thin out. 55 g. of the NJ 4 OH was then further added to maintain the pH at 7.
• the product has the following characteristics:
• Viscosity 11,500 cps.
• Example 3A The procedure of Example 3A was followed, using 87 ml NH 3 followed by 50 ml to maintain alkalinity. The solution was spun down several times and the pH was adjusted with 50% citric acid/aq NH 3 to about 7.2.
• Viscosity 17,000 cps.
• Example IA The procedure of Example IA was followed, and the product adjusted to pH 7.37 and spun down. The following characteristics were observed:
• Viscosity 9,500 cps.
• Example 3A The procedure of Example 3A was followed, initially using 100 ml NH 4 OH, and the pH adjusted to 7.0 with a further 10 ml. portion NH 4 OH.
• the product has the following characteristics:
• Example 3 The procedure of Example 3 was followed. The pH of the mixture was adjusted with 50% citric acid and NH 4 OH to 6.8 (as is). The product had the following characteristics:
• Example 2 The highly active alkyl ether sulfate half-ester obtained in Example 2 was evaluated against a commercial half-ester salt preparation. The results indicate that foam characteristics and viscosity potentiation are comparable.
• Alkyl ether sulfate half-ester 1 Standapol ESP Sauer ester sodium lauryl (C 12 -C 14 ) 2 EO sulfate.
• Alkyl ether sulfate half-ester 2 Standapol ES-1 Sauer ester sodium lauryl (C 12 -C 14l ) EO sulfate.
• Polyglycerol 3 Polyglycerol 06 6 mole oligomer of glycerol.
• Polyglycerol 6 Polyglycerol HOB257-26 6 mole oligomer of glycerol.
• StandamidTM LDS 8 lauric (C 12-18 ) diethanolamide.

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Cosmetics (AREA)
• Detergent Compositions (AREA)
• Polyethers (AREA)
• Polyesters Or Polycarbonates (AREA)
• Polysaccharides And Polysaccharide Derivatives (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Compositions Of Macromolecular Compounds (AREA)

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• 1988
  • 1988-04-12 US US07/180,408 patent/US4885379A/en not_active Expired - Fee Related
• 1989
  • 1989-04-11 EP EP89106434A patent/EP0337406B1/de not_active Expired - Lifetime
  • 1989-04-11 AT AT89106434T patent/ATE80159T1/de not_active IP Right Cessation
  • 1989-04-11 ES ES89106434T patent/ES2045233T3/es not_active Expired - Lifetime
  • 1989-04-11 DE DE8989106434T patent/DE68902672T2/de not_active Expired - Fee Related
  • 1989-04-12 JP JP1092787A patent/JPH0211699A/ja active Pending
  • 1989-04-12 AU AU32652/89A patent/AU611795B2/en not_active Ceased

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